Dean Gerard Winters (born July 20, 1964) is an American actor. He is known for his role as Ryan O'Reily on the HBO prison drama Oz and his roles in the TV series Millennium, Rescue Me, 30 Rock, Sex and the City, and Law & Order: Special Victims Unit, as well as portraying "Mayhem" in a series of Allstate Insurance commercials and starring in the 2014 film John Wick. He co-starred in one season of the CBS Network cop drama series Battle Creek and had a recurring role as "The Vulture" on the comedy series Brooklyn Nine-Nine. He also appeared in the 2023 Netflix film The Out-Laws and the 2024 AMC series Monsieur Spade.
Early life and education
Winters was born in New York City on July 20, 1964. He was raised on Long Island. He is of Irish and Italian descent, and speaks fluent Italian. Winters spent his teenage years in Scottsdale, Arizona. He attended Chaparral High School and graduated from Brophy College Preparatory, a Jesuit school in Phoenix, in 1982,
Winters performed stand-up comedy at Catch a Rising Star, The Comic Strip, and the Comedy Cellar alongside notable comedians Jerry Seinfeld, Paul Reiser, and Chris Rock. An HBO comedy special led him to the role he portrayed on Oz, the HBO-produced prison drama.
Winters was cast in the ABC drama pilot Happy Town, from the creators of October Road, but was replaced by Steven Weber after shooting the pilot.
Winters was away from acting until 2010, when Tina Fey brought him back to 30 Rock. Also that year, Winters was introduced as "Mayhem", a recurring character in a television and radio advertising campaign for Allstate Insurance created by the advertising agency Leo Burnett Chicago. In 2019, Fey joined Winters in a series of "Mayhem" commercials.
Winters played Avi in John Wick. Winters co-starred in one season of the CBS cop drama series Battle Creek, playing a small-town police force detective opposite Josh Duhamel, the FBI resident agent assigned to the town. The series was canceled in May 2015. He had a recurring role on Brooklyn Nine-Nine as The Vulture and had a supporting role as a divorce attorney on the HBO series Divorce.
In 2018, he was cast as Mr. Town in the second season of Starz's American Gods.
In 2019, he was in the film Framing John DeLorean.
Personal life
Winters has neuropathy, resulting in numbness and sensitivity issues in his hands and feet. In 2009, Winters contracted a bacterial infection and went into cardiac arrest. He underwent multiple surgeries and developed gangrene, resulting in the amputation of two of his toes and half of one of his thumbs.
Filmography
Film
{| class="wikitable sortable"
|-
! Year
! Title
! Role
! Notes
|-
| rowspan="2"|1997
| Conspiracy Theory
| Cleet
|
|-
| Lifebreath
| Chrystie's Lover
|
|-
| 1999
| Undercover Angel
| Harrison Tyler
|
|-
| rowspan="2" |2001
| Snipes
| Bobby Starr
|
|-
|Bullet in the Brain
|Bank Robber
|Short film
|-
| 2002
| Hellraiser: Hellseeker
| Trevor Gooden
| Direct to video
|-
| rowspan="2"|2004
| Brooklyn Bound
| Danny
|
|-
| Love Rome
| Dean
|
|-
| rowspan="2"|2006
| Bristol Boys
| Randy
|
|-
| Dead Calling
| Nick
|
|-
| 2007
| P.S. I Love You
| Tom
|
|-
| rowspan="3"|2009
| Winter of Frozen Dreams
| Ken Curtis
|
|-
| Splinterheads
| Reggie
|
|-
| Today's Special
| Steve
|
|-
| 2013
| The Devil You Know
| Jake Kelly
|
|-
| rowspan="2"|2014
| Don Peyote
| Gun Dealer
|
|-
| John Wick
| Avi
|
|-
| 2016
| Teenage Mutant Ninja Turtles: Out of the Shadows
| Bartender
|
|-
| 2017
| Rough Night
| Detective Frazier
|
|-
| rowspan="2"|2018
| After Everything
| Blake
|
|-
| Father of the Year
| Geoff
|
|-
| 2019
| Framing John DeLorean
| John Valestra
| Documentary
|-
| 2020
| Lost Girls
| Dean Bostick
|
|-
| rowspan="2"|2021
| Palmer
| Jerry
|
|-
| Christmas vs. the Walters
| Brian Walters
|
|-
| 2023
| The Out-Laws
| Vince Millen
|
|-
|rowspan="2" | 2024
|ZO
|Ryan O'Reily
|Short film
|-
| Justice League: Crisis on Infinite Earths - Part Three
| Captain Storm (voice)
| Direct-to-video
|-
| 2025
| Highest 2 Lowest
| Det. Higgins
|
|}
Television
{| class="wikitable sortable"
|-
! Year
! Title
! Role
! Notes
|-
| 1995–1996
| Homicide: Life on the Street
| Tom Marans
| 3 episodes
|-
| rowspan=2|1996
| NYPD Blue
| Larry
| Episode: "Where'd the Van Gogh?"
|-
| The Playroom
| Unknown
| rowspan="2" |Television film
|-
| 1997
| Firehouse
| Nick Wilkinson
|-
| 1997, 1999
| Millennium
| Young Michael Lanyard/Mr. Crocell
| 2 episodes
|-
| 1997–2003
| Oz
| Ryan O'Reily
| Main role, 56 episodes
|-
| 1998
| New York Undercover
| Paul Delaney
| Episode: "Rat Trap"
|-
| rowspan=2|1999
| Sex and the City
| John McFadden
| Episode: "The Fuck Buddy"
|-
| Saturday Night Live
| Ryan O'Reily
| Uncredited; Episode: "Jerry Seinfeld/David Bowie"
|-
| 1999–2000,<br/>2012–2014,<br/>2017–2019, 2025
| Law & Order: Special Victims Unit
| Detective Brian Cassidy
| Recurring role (seasons 1, 13–15, 19–20, 27), 32 episodes
|-
| 2001
| Deadline
| Des Lonegan
| Episode: "Shock"
|-
| rowspan=2|2002
| Third Watch
| Bill Stram
| Episode: "The Unforgiven"
|-
| The Twilight Zone
| Gordon
| Episode: "Future Trade"
|-
| 2004
| Strip Search
| Ned McGarth
| Television film
|-
| 2004–2007,<br/>2009, 2011
| Rescue Me
| Johnny Gavin
| Main role (seasons 1–4), 30 episodes; recurring role (seasons 5, 7), 3 episodes
|-
| 2005
| CSI: Miami
| Raymond Caine
| Episode: "10-7"
|-
| 2006, 2008–2012
| 30 Rock
| Dennis Duffy
| Recurring role, 15 episodes; <br>Nominated – Gold Derby Award for Best Guest Actor in a Comedy Series;<br/>Nominated – Online Film & Television Association Award for Best Guest Actor in a Comedy Series
|-
| 2008
| Law & Order: Criminal Intent
| Mike Stoat
| Episode: "Purgatory"
|-
| rowspan=2|2008–2009
| Terminator: The Sarah Connor Chronicles
| Charley Dixon
| Recurring role, 9 episodes
|-
| Life on Mars
| Vic Tyler
| 3 episodes
|-
| 2012
| Up All Night
| Casey Brinkley
| Episode: "Preschool Auction"
|-
| 2013
| Westside
| Robbie Carver
| Television film
|-
| 2013–2015,<br/>2017, 2019
| Brooklyn Nine-Nine
| Detective Keith 'The Vulture' Pembroke
| Recurring role, 9 episodes
|-
| 2014
| American Dad!
| Edward
| Voice role, episode: "News Glances with Genevieve Vavance"
|-
| 2015
| Battle Creek
| Russ Agnew
| Main role, 13 episodes
|-
| 2016
| Unbreakable Kimmy Schmidt
| Bunny
| Episode: "Kimmy Kidnaps Gretchen!"
|-
| 2016, 2018
| Divorce
| Tony Silvercreek
| Recurring role, 6 episodes
|-
| 2017, 2019
| Rapunzel's Tangled Adventure
| Andrew
| Voice role, 2 episodes
|-
| rowspan=4|2019
| Berlin Station
| Birdman
| Episode: "The Dream of the Four Policemen"
|-
| Wayne
| Daddy/Bobby Lucetti
| Recurring role, 6 episodes
|-
| American Gods
| Mr. Town
| Episode: "The Beguiling Man"
|-
| City on a Hill
| Ralph Hook
| Episode: "It's Hard to Be a Saint in the City"
|-
| 2021
| Girls5eva
| Nick
| 4 episodes
|-
| 2022
| Joe vs. Carole
| Jeff Lowe
| Miniseries, 3 episodes
|-
| rowspan=2|2024
| Monsieur Spade
| Father Morgan
| Miniseries, 2 episodes
|-
| So Help Me Todd
| Dick Franks
| 2 episodes
|-
|2026
| The Fall and Rise of Reggie Dinkins
| "FDNY: Chicago" Star
| Episode: "Put it on Your Cabbage!"
|}
References
External links
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